Ciramadol, Wy-15705
西拉马朵Chemical Name: (-)-(1R*,2R*)-2-[(R*)-alpha-(Dimethylamino)m-hydroxybenzyl]cyclohexanol; (-)-[1alpha(R*),2alpha]-3-[(Dimethylamino)-2(2-hydroxycyclohexyl)methyl]phenol
CAS No. 63269-31-8
项目整合开发状态: Phase III
项目研究机构: Wyeth Pharmaceuticals (Originator)
合成路线:The condensation of m-methoxybenzaldehyde (I) with cyclohexanone (II) by means of KOH in refluxing water gives m-methoxybenzalcyclohexanone (III),which by reaction first with dimethylamine (A) in ether and then reduction with LiAlH4 in the same solvent affords cis-2-(alpha-dimethylamino-m-methoxybenzyl)cyclohexanol (IV).The hydrolysis of (IV) with HCl in isopropanol yields the racemic product,which is finally resolved into the corresponding optical isomers with tartaric acid.
📌 参考资料/链接：
参考文献标题:Ciramadol
文献作者:Paton,D.M.; Castar,J.
参考来源:Drugs Fut 1980,5(6),283
📄 详细内容
合成路线:The condensation of m-methoxybenzaldehyde (I) with cyclohexanone (II) by means of KOH in refluxing water gives m-methoxybenzalcyclohexanone (III),which by reaction first with dimethylamine (A) in ether and then reduction with LiAlH4 in the same solvent affords cis-2-(alpha-dimethylamino-m-methoxybenzyl)cyclohexanol (IV).The hydrolysis of (IV) with HCl in isopropanol yields the racemic product,which is finally resolved into the corresponding optical isomers with tartaric acid.
参考文献标题:
文献作者:Yardley,J.P.; Russell,P.B.
参考来源:US 3928626
产品链接: CAS No. 63269-31-8››